IMO, the stiffness of the carbon sole in TR9 will not be noticeable over TR5's composite sole. The shoes seem equal otherwise. So I would go with TR5 and road shoe.

I have specialized S-Work and expert level road shoes and do not notice the difference between them myself.

If the high end tri shoe is the most comfortable, get that. I used nothing but tri shoes for 6 years, used shoe covers on cold days, and was fine. Just get whatever shoe fits the best and you can't go wrong there

Personally, I like the solid closure (ratchets, BOAs, laces) of a true road shoe for day-to-day. I only use my tri shoes for races.

As far as prices go, carbon soled shoes are definitely stiffer and marginally lighter; but really aren't any faster. I have some $$$$ Sidi Ergos, but my favorite road shoes are actually some LG laceups that were $69 at Performance (similar to the Giro Empires in look/fit, and due to the laces they are the same weight as the carbon Sidis which have the weight of the buckles): https://www.performancebike.com/...052_10551_1192565_-1

My advice is to get the tri shoes you like (may or may not be the most expensive). Use them for everything at the start and later get some dedicated road shoes if you want down the road. Cycling shoes last YEARS (I keep my average pair ~7), so get the shoes you'll love.

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ECMGN Therapy Silicon Valley:
Depression, Neurocognitive problems, Dementias (Testing and Evaluation), Trauma and PTSD, Traumatic Brain Injury (TBI)

Well, that's what I've ended up doing. Found a bargain on the last pair of Bont Riot TR's (~US$76) at bikebug. Fluro yellow, but I guess I can live with that :D

Summer's nearly here, so they should be fine for a while.